Methanol → HCID 67089447, compound

HRID 661088Notes

Reaction equation

HRID 661088 reaction equation
[C:1]([O:5][C:6]([C@@H:8]([C@@H:12]([C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1)/[CH:13]=[CH:14]/[CH3:15])[C:9]([OH:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[Si](C=[N+]=[N-])(C)(C)[CH3:29].CCCCCC>C1C=CC=CC=1>[C:1]([O:5][C:6]([C@@H:8]([C@@H:12]([C:16]1[CH:17]=[CH:18][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:20][CH:21]=1)/[CH:13]=[CH:14]/[CH3:15])[C:9]([O:11][CH3:29])=[O:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 67089197HCID 67089197, compound

Product 1

HCID 67089447HCID 67089447, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

(2S,3S,E)-2-(tert-butoxycarbonyl)-3-(4-(trifluoromethyl)phenyl)hex-4-enoic acid (5.3 g, 14 mmol) was taken up in 70 mL of 3.5:1 benzene:MeOH. TMS diazomethane, 2M in hexane (7.8 mL, 16 mmol) was added slowly to the mixture. Bubbling ensued. Approximately 2 mL excess TMS diazomethane reagent was added, presumably due to loss of titer of the reagent. The bubbling was monitored, and the addition was stopped when the bubbling ceased. The solvent was removed under reduced pressure. The mixture was triturated twice with 50 mL of 10% ether:hexanes, affording (2S,3S,E)-methyl 2-(tert-butoxycarbonyl)-3-(4-(trifluoromethyl)phenyl)hex-4-enoate (5.4 g, 98% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.59 (d, J=8.22 Hz, 2H) 7.34 (d, J=8.22 Hz, 2H) 5.75-5.59 (m, 2H) 4.92-4.84 (m, 1H) 4.70-4.63 (m, 1H) 3.78-3.72 (m, 1H) 3.68 (s, 3H) 1.72 (d, J=5.28 Hz, 3H) 1.37 (s, 9H).

Workup

  1. customBubbling
  2. additionApproximately 2 mL excess TMS diazomethane reagent was added, presumably due to loss of titer of the reagent
  3. additionthe addition
  4. customThe solvent was removed under reduced pressure
  5. customThe mixture was triturated twice with 50 mL of 10% ether

Sources & evidence

ORD record
ord-e5ed1098184a42a6a27912e0e01c58e9
Source dataset
uspto-grants-2011_12
Patent number
US08084479B2

Reaction notes

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